salicylic acid acetic acid acetylsalicylic acid (aspirin)

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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What type of reaction is this? It looks like some sort of Williamson Ether-looking synthesis, but involving phenols? How does the mechanism of this work? 

The image illustrates the chemical reaction involved in the synthesis of acetylsalicylic acid, commonly known as aspirin. This process is an esterification reaction where salicylic acid reacts with acetic acid in the presence of an acid catalyst (H⁺).

**Chemical Reaction:**

1. **Reactants:**
   - **Salicylic acid (left):** Contains a benzene ring attached to a carboxyl group (COOH) and a hydroxyl group (OH).
   - **Acetic acid (second from left):** Features a methyl group (CH₃) connected to a carboxyl group (COOH).

2. **Reaction Process:**
   - The presence of an acid catalyst (H⁺) facilitates the reaction.
   - The equilibrium sign indicates that this is a reversible process.

3. **Products:**
   - **Acetylsalicylic acid (right), or aspirin:** Produced by the esterification reaction. It has an ester group (O-C=OCH₃) replacing the hydroxyl group of salicylic acid.
   - **Water (H₂O):** Released as a by-product of the reaction.

This reaction demonstrates the formation of an ester linkage and is fundamental in the industrial production of aspirin.
Transcribed Image Text:The image illustrates the chemical reaction involved in the synthesis of acetylsalicylic acid, commonly known as aspirin. This process is an esterification reaction where salicylic acid reacts with acetic acid in the presence of an acid catalyst (H⁺). **Chemical Reaction:** 1. **Reactants:** - **Salicylic acid (left):** Contains a benzene ring attached to a carboxyl group (COOH) and a hydroxyl group (OH). - **Acetic acid (second from left):** Features a methyl group (CH₃) connected to a carboxyl group (COOH). 2. **Reaction Process:** - The presence of an acid catalyst (H⁺) facilitates the reaction. - The equilibrium sign indicates that this is a reversible process. 3. **Products:** - **Acetylsalicylic acid (right), or aspirin:** Produced by the esterification reaction. It has an ester group (O-C=OCH₃) replacing the hydroxyl group of salicylic acid. - **Water (H₂O):** Released as a by-product of the reaction. This reaction demonstrates the formation of an ester linkage and is fundamental in the industrial production of aspirin.
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